


Truth or Dare

by TobytheWise



Series: 1k Celebration [29]
Category: Supernatural
Genre: Anal Fingering, Bottom Castiel (Supernatural), Friends to Lovers, Frottage, Getting Together, Love Confessions, Multi, Truth or Dare
Language: English
Status: Completed
Published: 2019-08-21
Updated: 2019-08-21
Packaged: 2020-09-23 13:34:46
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,304
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/20340952
Author URL: https://archiveofourown.org/users/TobytheWise/pseuds/TobytheWise
Summary: The one where Cas, Benny, and Dean finally get together during a tipsy game of Truth or Dare.





	Truth or Dare

**Author's Note:**

> Written for Anon for my 1k celebration <3

Dean picks up the bottle of whiskey. His head tilts back towards the ceiling as he takes a large swig. It burns his throat in a familiar way which he loves. His best friends sit around his shitty little coffee table. 

“My turn,” Cas says, taking the bottle and drinking. Dean tries not to stare at Cas’ throat as he swallows. He fails miserably. 

Cas hands the bottle over to Benny with a smile. He tilts it back, only coughing a little. It’s cute how the bear of their little group is the one to have a problem with his liquor.

The three of them have been best friends since junior year of high school. They’ve been through thick and thin and always come out the otherside closer. Not quite as close as Dean would prefer but he shoves those feelings down. As always. Because who is he to have feelings for not one but both of his best friends?

Dean slaps his hands together. “Alright, boys,” he says, taking the whiskey back. “Usual rules are in play. If you don’t wanna answer or don’t wanna do the dare, you drink.”

“Hot Wings,” Benny says, kicking his foot against Cas’ thigh. “Truth or dare?”

Cas shoves right back, smiling over at Benny. “Truth.”

“Starting the game conservative. Not surprising,” Benny teases. “Alright, brother, why’d you actually break up with Meg?”

Cas turns towards the bottle of whisky in the middle of the coffee table for a moment, contemplating. Finally he sighs. “I just didn’t have feelings for her. I was-” he rubs his face. “I was pining and we both knew it.”

Before either he or Benny can comment, Cas’ blue eyes turn to Dean. “Truth or dare?”

Dean gives Cas his best smirk before declaring, “dare.”

Cas cocks a brow at Benny, making Dean’s belly flutter. “I dare you,” he says, his deep voice sounding thoughtful. “I dare you to drink one of those funky shakes that Benny keeps in the fridge.”

Dean groans. He hates coping out of dares but he’s gotta put his foot down! Dean slowly leans forward, picking up the whiskey bottle. “Really?” Benny whines. “My shakes are worse than not taking a dare?”

Dean laughs before taking a drink, setting the bottle down with a sigh. “I’d rather lose this entire game than drink one.”

Benny crosses his arms over his chest. Dean’s eyes are drawn to the way his shirt stretches around Benny’s large biceps. Fuck. Maybe those nasty shakes and morning workouts really are worth it if those guns are the results. 

“Benny, truth or dare.”

Benny leans back in his chair, the picture of ease as he answers. “Truth.”

Dean swallows, the bit of alcohol in his system making him bold. “Do you think Cas is hot?”

Dean watches as Benny looks over at Cas. His heart speeds up in his chest. Cas bites his bottom lip, waiting for Benny to answer. “Yeah,” he finally says, his cheeks turning a pretty pink where it peeks out from under his beard. “For some reason I’m attracted to you,” he says with a shrug. 

Dean wonders if it’s normal to feel relief at the declaration, rather than jealousy. In his wildest dreams, he fantasizes about them both, together, with him. 

The room feels charged with energy as Cas smiles over at Benny. “Dean,” Benny says, pulling his eyes away from Cas. “Truth or dare?”

“Truth,” he says, licking his lips, delighted to realize two pairs of eyes following the movement. 

“Those panties I found in your laundry? Those weren’t a girl’s, were they?”

Dean’s cheeks turn bright red as he looks down between his feet. He debates lying. But then he thinks about Benny just telling the truth and decides to just spill the beans. “They’re mine.”

He looks up, finding Benny adjusting his pants as Cas stares with undisguised lust. Fuck. Could this really be happening or is this his imagination playing tricks on him, making him see what he so desperately wants to see?

“Cas,” he says, his voice coming out huskier than before. “Truth or dare?”

“Dare.”

Dean sucks in a shaky breath. His eyes flick over to Benny before turning back to Cas. “I dare you to kiss Benny.”

Benny gasps. “I couldn’t,” Cas says. “It wouldn’t be fair to Benny.”

Before Dean can say anything, Benny’s leaning forward. “It’s okay. I don’t mind,” he whispers. 

Dean sits stock still as Cas slowly leans over towards Benny, Benny doing the same towards Cas. Dean holds his breath, their eyes staring at one another. Benny’s big hand cups Cas’ cheeks as their lips meet. It starts chaste, just the slow press of lips until Cas opens his mouth. Benny groans as he opens as well. Dean sees pink peek out as their tongues touch and he has to bite his lip to stifle a whimper. Fuck, they’re so sexy together! 

When they slowly pull away, they’re both flushed pink, their breathing strained. Do they have any idea what they’ve just done to Dean? As subtle as possible, he adjusts his hard cock. 

Dean sits back, watching as the two sit there in a daze. Cas’ finger touches his lips, like he can’t believe that just happened. His eyes flick up to meet Dean’s gaze. He clears his throat before whispering, “Dean, truth or dare?”

Dean swallows around the lump in his throat. His eyes flick between Cas and Benny, both sets of eyes watching him with an intensity that makes his body break out in goosebumps. 

“Dare.”

“Strip down to your boxers,” Benny blurts out. 

He freezes until Cas says, “yeah. Do that.”

Dean blushes as he slowly pulls his t-shirt over his head. His flush is running down the middle of his chest but by the looks he’s getting from Cas and Benny, they like the look of it. He stands up, his hands going to the top of his jeans. He ignores the way his hands shake when he unbuttons his pants. 

Suddenly, there are hands touching his own. Dean looks up, sucking in a breath as his eyes meet Benny’s beautiful blue ones. Benny’s on his knees before Dean, his hands gently pushing Dean’s away. 

“Let me,” he whispers. 

Dean nods, moving his hands and watching as Benny slowly opens his jeans, pulling them down. His gaze raises over Benny’s head, meeting Cas’ eyes. He watches on, a tiny smile on his lips, like maybe he’s enjoying the two of them together. The same way Dean loved seeing Cas and Benny kiss. Hope floods Dean’s chest. 

Dean’s skin prickles as he’s exposed to the cool air. Benny’s hands run up his thighs before he realizes what he’s doing and pulls back. Dean tries not to let too much disappointment show on his face. 

“Truth or dare?” Dean asks Benny, his voice barely above a whisper. He’s terrified of breaking whatever spell is going on inside this room, so scared of shattering what they’re making. 

“Truth.”

Dean licks his lips before whispering. “Have you ever thought about this? About us?” He pauses. When he speaks again, the room somehow grows even more silent. “All together.”

Benny turns to look at Cas before his eyes turn towards the ground. “Yes,” he breathes out, his shoulders tensing like he’s waiting for argument or hate. But instead, Dean breathes a sigh of relief. 

“Me too,” he says. 

Cas clears his throat, his voice coming out husky when he finally speaks. “I have as well. For years.”

It’s like a rubber band has been stretched too far and has finally snapped. Dean and Cas move at the same time, crowding up against Benny on both sides. His big arms wrap around their waists. 

“I wanna see you two kiss,” Cas murmurs, his eyes lidded with lust. 

Dean smiles before pulling Benny into a kiss. His lips are soft against his own. When Benny’s tongue enters his mouth, his body breaks out in goosebumps. Cas’ hand runs over his back and it makes Dean feel complete and perfect. 

Benny pulls back. His hands push together until Dean and Cas are chest to chest and Dean gets the idea. He leans forward, placing their lips together. Cas’ lips are more chapped than Benny’s and he’s more aggressive with his kisses. It’s hot and perfect and has Dean’s cock blurting precum. 

“I feel like you two are overdressed,” Dean murmurs.

“Agreed,” Cas says, his hands going to Benny’s shirt. Dean and Cas take their time, slowly peeling Benny’s layers away until he’s naked, completely bare for them. His broad chest on display, showing off the miles of skin Dean wants to get his hands on. His erection is thick and long, standing up towards his belly. 

“Your turn,” Benny says, his eyes predatory as he gazes as Cas. 

Dean falls to his knees, working on releasing Cas from his pants and boxers as Benny helps him with his shirt. Once he’s naked, Dean can’t help himself, he runs his tongue over Cas’ erection. Cas lets out a groan as Benny’s hand finds the back of Dean’s head. All three connected. 

“Fuck,” Cas hisses as Dean takes him fully into his mouth. “Your mouth, Dean.”

Dean moans, the vibrations running through Cas’ cock, rewarding him with the first taste of Cas’ precum. It’s so good and he takes his time lapping it up, savoring it. 

“Let Benny feel how good your mouth is,” Cas says, running a thumb over Dean’s cheek. 

Dean pulls off as Cas pushes his face towards Benny’s erection. He opens his mouth, his eyes locking with Benny’s as he slowly feeds his cock into Dean’s mouth. His dick is thicker than Cas’ but still fits perfectly in Dean’s mouth, the musky taste making him drool and desperate for more. 

His eyes look up, watching as Benny and Cas exchange kisses back and forth. Fuck, Dean could sit down here and watch that all day. His hand wraps around his own erection, slowly sliding up and down. 

“God,” Cas says, pulling Dean up by his hair, taking his lips in a fierce and messy kiss. “I want someone inside of me so fucking bad. Please?”

Benny groans at Cas’ words while Dean stills, his cock throbbing between his legs. Benny kisses Cas’ lips before kissing Dean’s and running off towards his room. 

Dean grabs Cas around his waist, pulling him towards the couch before pulling him down onto his lap. The warm weight of Cas on top of Dean has him groaning, his hips riding up and rubbing his cock against Cas’ toned abs. 

“I can’t believe this is happening,” Dean murmurs as Cas begins kissing his throat. His hands grip Cas’ hips, not forcing him to move, just holding him right where he is. 

“Got it!” Benny cheers, walking back into the room, holding up a bottle of lube. He gets on his knees behind Cas. Cas whimpers at whatever Benny is doing and the sound goes right to Dean’s cock. 

“Oh god, oh god,” Cas murmurs, shoving his hips back towards Benny. Dean takes each of Cas’ ass cheeks in his hands, squeezing hard before pulling them apart, opening him up for Benny. 

“Fuck, Hot Wings,” Benny murmurs. From over Cas’ shoulder, Dean can tell he’s staring at Cas’ hole. Benny squirts some lube onto his fingers before bringing them to Cas’ ass. 

“Yes,” Cas hisses. Dean reaches up, taking Cas by the back of the head, pulling him into a kiss. They make out as Benny fingers Cas’ ass, Cas whimpering into Dean’s mouth whenever he hits Cas’ prostate. Dean moves his hips, rubbing their hard cocks together. 

“Oh fuck, baby,” Dean murmurs, staring up at Cas’ flushed face. “Look at you.”

“I love it,” Cas hisses, his head tilted back towards the ceiling. “Love feeling something inside me.” He lets out a high pitched whine that makes Dean think that Benny just added another finger. “Fuck. Love feeling full.”

Dean reaches back, finding Cas’ ass stretched around Benny’s fingers. He looks at Benny before smirking and adding one of his own fingers to Cas’ hole. “You feel that,” he whispers huskily into Cas’ ear. “Now we’re both inside of you.”

“Oh god,” Cas cries, his cock twitching between them. Cas reaches down, taking them both into his hand, stroking them hard and fast. 

“Shit, shit,” Dean whimpers. “Not gonna last long like that.”

“Jesus,” Benny says, nibbling the back of Cas’ shoulders. “You two look so incredible together. So sexy.” He pauses before adding, “all mine.”

It’s enough to have Dean throwing his head back, crying out as he comes. Cas’ hand tightens around them, prolonging his pleasure. The heat around his finger tightens before Cas is coming as well, adding more mess between their bellies. 

“Oh fuck,” Benny murmurs. Dean gently pulls his finger from Cas’ ass, wrapping his hand around Benny’s erection instead. 

“Come on, Benny,” Cas whines, thrusting his ass back. “Come on me. Please.”

Benny bites his bottom lip as he thrusts into Dean’s hand before coming across Cas’ lower back and ass. It’s the hottest experience Dean’s ever had. 

Before his worries can get the best of him, Cas is leaning down, running his nose over Dean’s. “I know what’s going through that beautiful mind of yours,” Cas murmurs softly. “But this isn’t a one time thing. At least, I don’t want it to be.”

“Neither do I,” Benny says over Cas’ shoulder. “This is real.” He swallows. “I love you. Both of you.”

“I’m the luckiest son of a bitch alive,” Dean says with wide smile, pulling both of his men into his arms. He doesn’t even care that it’s awkward as fuck because he’s just so incredibly happy. And to think, this is only the beginning.


End file.
